2-<(2-carbometoxyethyl)thio>indole | 139461-64-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-<(2-carbometoxyethyl)thio>indole
• 英文别名: methyl 3-(2-indolylthio)propionate；methyl 3-(1H-indol-2-ylsulfanyl)propanoate
• CAS: 139461-64-6
• 化学式: C₁₂H₁₃NO₂S
• 分子量: 235.307
• InChiKey: JRVXKVGFEPKMTH-UHFFFAOYSA-N

物化性质

• 沸点：
  417.0±25.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<(2-carbometoxyethyl)thio>indole 在 lithium aluminium deuteride 、 甲烷磺酸 、 乙基溴化镁 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 0.55h， 生成 <4-²H2>-2,3,4,9-tetrahydrothiopyrano<2,3-b>indole
  参考文献：
  名称：

  Ishizuka, Natsuki, Journal of the Chemical Society. Perkin transactions I, 1990, # 4, p. 813 - 826

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-bis<(2-carbomethoxyethyl)thio>indole 在 硫代水杨酸 作用下， 以 三氟乙酸 为溶剂， 反应 1.0h， 以80%的产率得到2-<(2-carbometoxyethyl)thio>indole
  参考文献：
  名称：

  Nonreductive Desulfenylation of 3-Indolyl Sulfides. Improved Syntheses of 2-Substituted Indoles and 2-Indolyl Sulfides

  摘要：

  Desulfenylation of 3-indolyl sulfides to the corresponding 3-unsubstituted indoles is usually carried out under reductive conditions, thus accommodating only substituents which are resistant to reduction. We have developed a nonreductive procedure for removal of a sulfide at the 3-position of indoles, using trifluoroacetic acid in the presence of a thiol as trapping agent, which is compatible with a large array of functionalities on the indole ring. In addition, the desulfenylation occurs selectively at the 3-position of the indole, and sulfide groups at other positions of the molecule remain untouched. Thus, indole 2,3-bis-sulfides are selectively desulfenylated at the 3-position, affording 3-unsubstituted 2-indolyl sulfides. This methodology broadens the use of sulfide as a protecting group for the 3-position of indoles.

  DOI：

  10.1021/jo00100a045

文献信息

• Acid-catalyzed isomerization of 3-indolyl sulfides to 2-indolyl sulfides: first synthesis of 3-unsubstituted 2-arylthioindoles. Evidence for a complex intermolecular process
  作者：Pierre Hamel、Yves Girard、Joseph G. Atkinson

  DOI：10.1021/jo00035a029

  日期：1992.4

  The acid-catalyzed isomerization of 3-indolyl sulfides 1 to the corresponding 2-indolyl sulfides 4 provides the first synthesis of 3-unsubstituted 2-(arylthio)indoles, a hitherto unattainable class of compounds. When catalyzed by trifluoroacetic acid, the isomerization proceeds mainly via an intermolecular mechanism involving initial disproportionation to a 2,3-indolyl bis-sulfide 5 and an unsubstituted counterpart 6 followed by further interaction of these species to yield the rearranged isomer 4. A mechanism is proposed involving a role for the acid in the sulfenyl-transfer steps. This type of process also occurs, to a lesser extent, in the polyphosphoric acid catalyzed isomerization.
• ISHIZUKA, NATSUKI, J. CHEM. SOC. PT 1. PERKIN TRANS.,(1990) N, C. 813-826
  作者：ISHIZUKA, NATSUKI

  DOI：——

  日期：——
• Nonreductive Desulfenylation of 3-Indolyl Sulfides. Improved Syntheses of 2-Substituted Indoles and 2-Indolyl Sulfides
  作者：Pierre Hamel、Nicolas Zajac、Joseph G. Atkinson、Yves Girard

  DOI：10.1021/jo00100a045

  日期：1994.10

  Desulfenylation of 3-indolyl sulfides to the corresponding 3-unsubstituted indoles is usually carried out under reductive conditions, thus accommodating only substituents which are resistant to reduction. We have developed a nonreductive procedure for removal of a sulfide at the 3-position of indoles, using trifluoroacetic acid in the presence of a thiol as trapping agent, which is compatible with a large array of functionalities on the indole ring. In addition, the desulfenylation occurs selectively at the 3-position of the indole, and sulfide groups at other positions of the molecule remain untouched. Thus, indole 2,3-bis-sulfides are selectively desulfenylated at the 3-position, affording 3-unsubstituted 2-indolyl sulfides. This methodology broadens the use of sulfide as a protecting group for the 3-position of indoles.
• Ishizuka, Natsuki, Journal of the Chemical Society. Perkin transactions I, 1990, # 4, p. 813 - 826
  作者：Ishizuka, Natsuki

  DOI：——

  日期：——